Frank Sinatra, born on December 12, 1915, in Hoboken, New Jersey, was an iconic American singer, actor, and cultural icon. Known as “The Voice,” Sinatra’s smooth and velvety vocal style, combined with his impeccable phrasing and emotional delivery, made him one of the greatest interpreters of popular music in the 20th century.
Sinatra’s career spanned over six decades, beginning in the 1930s as a vocalist for various big bands and orchestras. He achieved immense success as a solo artist in the 1940s, becoming one of the most popular and influential singers of his time. Sinatra’s renditions of classic standards like “Fly Me to the Moon,” “My Way,” “New York, New York,” and “Strangers in the Night” are timeless and have become synonymous with his name.
Sinatra’s musical style embraced various genres, including swing, jazz, traditional pop, and later, even rock and roll. His ability to infuse emotion into every lyric and capture the essence of a song made him a masterful storyteller. Sinatra’s voice was rich, expressive, and had a unique ability to evoke feelings of love, longing, and melancholy.
Aside from his musical career, Sinatra also made a significant impact in the film industry. He starred in over 60 films, including acclaimed performances in movies like “From Here to Eternity,” for which he won an Academy Award for Best Supporting Actor, and “The Manchurian Candidate.” His charismatic on-screen presence and undeniable talent made him a respected actor in addition to his status as a legendary singer.
Sinatra’s influence extends far beyond his music and films. He was a cultural icon and trendsetter, known for his suave persona, impeccable style, and association with the Rat Pack—a group of entertainers that included Dean Martin, Sammy Davis Jr., and others. Sinatra’s popularity and influence reached international levels, and his music remains beloved by fans of all generations.
Throughout his life, Sinatra’s career had its ups and downs, but he always managed to stage remarkable comebacks. His resilience and determination to succeed, combined with his extraordinary talent, solidified his status as one of the greatest entertainers of all time.
Frank Sinatra’s legacy is undeniable. His contributions to popular music, his impact on American culture, and his enduring appeal as an artist continue to resonate today. His voice and the emotions he conveyed through his songs touched the hearts of millions, and his influence on subsequent generations of musicians is immeasurable. Frank Sinatra’s name will forever be synonymous with timeless music, style, and the epitome of cool.
1. “Softly, As I Leave You”
Sinatra's "Softly, As I Leave You" is a top-notch tune. It paints a picture of bittersweet memories and goodbyes with poise and feeling. It starts off with some soft piano chords, then Sinatra's velvet voice takes you back in time, to a place full of nostalgia and sorrow. The song speaks of a love gone by, but it still cherishes the moments they shared.
As the song carries on, strings surge with emotion towards the close, leaving you in a thoughtful trance. It's one of his most genuine and passionate pieces, making it one of the greatest Frank Sinatra songs of all time.
It's interesting to note, the idea for the song came from a conversation between Sinatra and his daughter, about her departing home for college. The words "softly as I leave you" stayed with him, which led to the creation of this timeless classic. Sinatra's smooth singing could charm anyone, except maybe the unfortunate Valentine in this heartbreaking ballad.
2. “My Funny Valentine”
"My Funny Valentine" is a classic that displays Sinatra's skill to interpret popular songs with suavity. Rodgers and Hart wrote it first for the 1937 musical comedy "Babes in Arms."
Sinatra's version of this jazz standard charms listeners with its meaningful lyrics. They say love isn't perfect, yet still real. Sinatra's rendition impresses. He begins like he's unable to vocalize his lover's flaws. But when somebody praises her, he understands how he can admire her imperfections. The tune creates freedom with each note. Funky drums, effervescent brass, and his soft lyrical tone join together perfectly. Every buildup leads to a conclusion you can dance on.
It's said that during WW2, soldiers played "My Funny Valentine" before going off to war. They imagined their Valentines back home in silver light. This music today makes us remember our own funny Valentines. Frank shows he's no conformist with 'The Lady is a Tramp'.
3. “The Lady is a Tramp”
Frank Sinatra's "The Lady is a Tramp" is an iconic classic that still resonates with listeners today. It was originally written for the Broadway musical "Babes in Arms" by Rodgers and Hart. Sinatra's version was rewritten to include a male voice.
What makes this song unique is its take on societal norms. It mocks high society and celebrates independent women who don't conform to anyone's ideals.
This timeless classic is perfect for a night out with friends or while driving down the scenic countryside. Its upbeat tempo will have you singing along to the witty lyrics.
It's impossible to think of New York without this Sinatra classic playing in your head!
4. “New York, New York”
New York City, the Big Apple, is iconic. Frank Sinatra's song "New York, New York" immortalizes it. It was first in a film of the same name, directed by Martin Scorsese. Its upbeat tempo and captivating lyrics capture the vibrant hustle and bustle of the city. It's an anthem for locals and visitors alike. Sinatra's vocal range and connection with his audience make it a hit.
Fun fact: It was written as a theme for Liza Minnelli. But it was Sinatra's version that became famous. Take a flight with Sinatra and "Come Fly With Me". Don't forget to buckle up!
5. “Come Fly With Me”
Frank Sinatra's “Come Fly With Me” is iconic – a journey of sound that stands the test of time. It opens with a soaring brass section, and Sinatra's vocals capture the adventure of travelling and experiencing different cultures. Clever wordplay and witty lyrics showcase his storytelling skills.
The song switches between genres, from a big-band swing to a bossa nova-inspired break. This creates a dreamy feel and keeps it interesting. Add the song to your playlist for a touch of nostalgia and timelessness.
Seen in movies like Catch Me If You Can and Mad Men, it is the perfect soundtrack for any party or event.
Let Sinatra take you on an adventure! Listen to “Come Fly With Me” today. You'll feel like you can fly, even if you're just sitting on your couch.
6. “Fly Me to the Moon”
This Sinatra classic captures the essence of crooning. Its smooth melody and nostalgic feel, "Fly Me to the Moon" transports listeners to a romantic and elegant era. The dreamy lyrics talk about escaping to outer space with a beloved. It's no wonder this song has been covered by many artists.
What makes this song unique is its simplicity. The arrangement is stripped down, so Frank's voice stands out. The rhythm section and the twinkling piano create an ethereal atmosphere that fits the romantic lyrics.
An interesting fact about "Fly Me to the Moon" is that it was originally named "In Other Words." Bart Howard wrote the song in 1954, but it was Sinatra's version from 1964 that became a hit.
Pro Tip: To impress your friends with karaoke, this is your song. The melody might seem easy, but those high notes require practice. Sinatra has us all under his spell, and who wouldn't want his smooth vocals captivating them?
7. “I’ve Got You Under My Skin”
This timeless tune is one of Frank Sinatra's most cherished songs. "I've Got You Under My Skin" was released in 1956 and quickly became a hit with fans around the globe. The song has withstood the test of time and is still a popular choice for covers today.
The song speaks of a man's infatuation with a woman, portraying the universal difficulty of being haunted by past relationships. The melody is catchy and memorable, with big band instrumentation perfectly complementing Sinatra's signature vocals.
What makes this song special is its ever-lasting charm across generations. It has been covered by many artists, including Michael Bublé, Diana Krall and Tom Jones, each offering their own unique version of the classic.
Rumor has it that when composer Cole Porter was asked to name his favorite composition, he famously answered, "Anything but 'I’ve Got You Under My Skin'". Despite this humorous remark, it remains one of Sinatra's most iconic tunes and has cemented his place as one of the greatest crooners of all time. Sinatra's crooning in 'The Way You Look Tonight' will transform any ugly cry into a beautiful masterpiece.
8. “The Way You Look Tonight”
"The Way You Look Tonight" – a classic unrequited love song. Frank Sinatra's iconic version captures the essence of being in love. Its gentle melody, heartfelt lyrics and charming voice make you feel all warm and fuzzy inside. It won an Academy Award for Best Original Song in 1936.
Jerome Kern crafted this tune to stand the test of time. He avoided slang or cultural references so it could be meaningful across generations. This song has become a beloved standard. Sinatra's interpretation adds to its timelessness.
"The Way You Look Tonight" was originally written for a movie. Fred Astaire performed it while dancing with Ginger Rogers. Decades later, Sinatra made it his own with his vocal style and dramatic storytelling. He showcased his ability to deliver a performance filled with emotion, cementing his legacy.
Even if you're not a Sinatra fan, this song will make you feel like a suave detective. Don't forget your fedora!
9. “Strangers in the Night”
Frank Sinatra's "Strangers in the Night" is a memorable track. His charismatic voice and Nelson Riddle's orchestral arrangement make it a beautiful tune. It won 3 Grammys and became one of Sinatra's most successful songs.
The lyrics talk about two strangers who embrace unexpected feelings. It has catchy tunes and beats. This track highlights Sinatra's singing talent. It's been remade by many artists, showing its influence. Genres like jazz, pop rock and soul make it timeless.
If you want to play it at an event or wedding, dim lighting and Sinatra's classic style fashion accessories like hats and suspenders will create a surreal atmosphere. Sinatra's 'My Way' is also the perfect song to play at funerals!
10. “My Way”
No list of the 10 Best Frank Sinatra Songs of All Time is complete without "My Way." This ballad is worldwide renowned for its thought-provoking message about living life your own way.
The song speaks of looking back on life with pride, in spite of mistakes. It emphasizes that everyone makes missteps, but they should remain true to themselves. That's what makes it stand out from other Sinatra songs.
Its grand yet personal arrangement makes it ideal for weddings, festivals, and even funerals. It's a reminder to live life to the fullest – whatever that means for you.
If you ever feel low or uncertain, listen to "My Way" for motivation. Take Frank's words to heart and strive to make the most of your life. This song has spawned countless covers and will continue to inspire for years to come.
Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
